Acetic Acid → (R)-3-{4-[(4-tert-butylphenylamino)methyl]benzoylamino}-2-hydroxypropionic acid

HRID 967672Notes

Reaction equation

HRID 967672 reaction equation
[CH:1]([C:3]1[CH:17]=[CH:16][C:6]([C:7]([NH:9][CH2:10][C@@H:11]([OH:15])[C:12]([OH:14])=[O:13])=[O:8])=[CH:5][CH:4]=1)=O.[C:18]([C:22]1[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=1)([CH3:21])([CH3:20])[CH3:19].C(O)(=O)C.C([BH3-])#N.[Na+]>CN1CCCC1=O.COC(OC)OC.CO>[C:18]([C:22]1[CH:23]=[CH:24][C:25]([NH:26][CH2:1][C:3]2[CH:17]=[CH:16][C:6]([C:7]([NH:9][CH2:10][C@@H:11]([OH:15])[C:12]([OH:14])=[O:13])=[O:8])=[CH:5][CH:4]=2)=[CH:27][CH:28]=1)([CH3:21])([CH3:19])[CH3:20]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 698614-Tert-ButylanilineHCID 5003444Sodium cyanoborohydrideHCID 86586064(R)-3-(4-Formylbenzoylamino)-2-hydroxypropionic acid

Product 1

HCID 69733516(R)-3-{4-[(4-tert-butylphenylamino)methyl]benzoylamino}-2-hydroxypropionic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 9005Trimethyl orthoformateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

The above resin bound (R)-3-(4-formylbenzoylamino)-2-hydroxypropionic acid was treated with a 0.5 M solution of 4-tert-butylaniline (0.25 mmol) in a mixture of N-methyl-2-pyrrolidinone and trimethylorthoformate (1:1, 0.5 mL) and glacial acetic acid (50 μL) for 1 hour at 25° C. Sodium cyanoborohydride (250 μmol, 16 mg) dissolved in a mixture of N-methyl-2-pyrrolidinone and methanol (1:1, 0.25 mL) was added and the mixture was vortexed at 25° C. for 4 hours followed by filtration and washing with a mixture of N-methyl-2-pyrrolidinone and methanol (1:1, 2×1 mL) 3×1 mL N-methyl-2-pyrrolidinone (3×1 mL) and a mixture of 1,2-dichloropropane and diisopropylethylamine (7:1, 2×0.75 mL).

Workup

  1. additionwas added
  2. filtrationfollowed by filtration
  3. washwashing with a mixture of N-methyl-2-pyrrolidinone and methanol (1:1, 2×1 mL) 3×1 mL N-methyl-2-pyrrolidinone (3×1 mL)
  4. additiona mixture of 1,2-dichloropropane and diisopropylethylamine (7:1, 2×0.75 mL)

Sources & evidence

ORD record
ord-b5a2198e6cbc46909f87db4ea88f8bf4
Source dataset
uspto-grants-2005_10
Patent number
US06953812B2

Reaction notes

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